Styrene Oxide → HCID 178477571, compound

HRID 853136Notes

Reaction equation

[CH:1]1([CH2:4][NH:5][C@H:6]2[CH2:11][CH2:10][C@H:9]([C:12]([O:21][Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.Cl([O-])(=O)(=O)=O.[Li+].[C:35]1([CH:41]2[O:43][CH2:42]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[NH4+].[Cl-]>C(#N)C.CCOCC>[CH:1]1([CH2:4][N:5]([C@H:6]2[CH2:7][CH2:8][C@H:9]([C:12]([O:21][Si:22]([CH2:25][CH3:26])([CH2:27][CH3:28])[CH2:23][CH3:24])([C:13]([F:16])([F:15])[F:14])[C:17]([F:18])([F:19])[F:20])[CH2:10][CH2:11]2)[CH2:42][CH:41]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[OH:43])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 100 mg (0.23 mmol) of trans cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine (example 24.2) in 0.5 mL of acetonitrile was treated with 41 mg (0.38 mmol) of lithiumperchlorate and 46 mg (0.38 mmol) of (rac) phenylethylenoxide. The mixture was stirred in a sealed tube at 80° C. for 6 hrs and distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4, evaporation of the solvent and column chromatography on silica gel with heptane/EtOAc 1:1 gave 52 mg (49%) of (rac) trans 2-{cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amino}-1-phenyl-ethanol as a colorless oil, MS: 554 (M+H)+.

Workup

dry with materialDrying of the combined organic phases over Na2SO4, evaporation of the solvent and column chromatography on silica gel with heptane/EtOAc 1:1

Sources & evidence

ORD record: ord-78bf2efea0384e18a4e0130d7abc54dd
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253282B2

Reaction notes

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